Crystal structure of 2-methyl­amino-3-nitro-4-p-tolyl­pyrano[3,2-c]chromen-5(4H)-one

Govindaraj, J.; AaminaNaaz, Y.; Kamalraja, J.; Perumal, P.T.; SubbiahPandi, A.

doi:10.1107/S205698901500225X

organic compounds

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ISSN: 2056-9890

Volume 71| Part 3| March 2015| Pages o158-o159

doi:10.1107/S205698901500225X

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Crystal structure of 2-methylamino-3-nitro-4-p-tolylpyrano[3,2-c]chromen-5(4H)-one

J. Govindaraj,^a Y. AaminaNaaz,^b Jayabal Kamalraja,^c Paramasivam T. Perumal ^c and A. SubbiahPandi ^b ^*

^aDepartment of Physics, Pachaiyappa's College for Men, Kanchipuram 631 501, India, ^bDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India, and ^cOrganic Chemistry Division, Central Leather Research Institute, Adyar, Chennai 602 020, India
^*Correspondence e-mail: aspandian59@gmail.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 21 December 2014; accepted 3 February 2015; online 7 February 2015)

In the racemic title compound, C₂₀H₁₆N₂O₅, the pyran ring adopts a shallow envelope conformation, with the stereogenic C atom displaced from the other atoms by 0.273 (2) Å. The dihedral angle between the fused-ring system and the pendant p-tolyl group is 87.62 (7)°. The molecular conformation is consolidated by an intramolecular N—H⋯O hydrogen bond, which generates an S(6) ring. In the crystal, molecules are linked by C—H⋯O interactions, resulting in [010] chains.

Keywords: crystal structure; pyrano[3,2-c]chromenone; biological activity; chromene derivatives; hydrogen bonding; crystal structure.

CCDC reference: 1046918

1. Related literature

For background to the biological activity of chromene derivatives, see: Borges et al. (2005 , 2009 ); Gibbs (2000 ); Varmus (2006 ). For a related structure, see: Narayanan et al. (2013 ).

2. Experimental

2.1. Crystal data

C₂₀H₁₆N₂O₅
M_r = 364.35
Monoclinic, P 2₁ /n
a = 10.8336 (11) Å
b = 11.7927 (11) Å
c = 13.7275 (14) Å
β = 108.357 (2)°
V = 1664.5 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 293 K
0.21 × 0.19 × 0.18 mm

2.2. Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.978, T_max = 0.981
28712 measured reflections
4571 independent reflections
2862 reflections with I > 2σ(I)
R_int = 0.039

2.3. Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.151
S = 1.03
4571 reflections
244 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O5	0.86	1.96	2.590 (2)	129
C9—H9C⋯O4ⁱ	0.96	2.46	3.389 (3)	163
Symmetry code: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 1046918

Crystal structure: contains datablocks global, I. DOI: 10.1107/S205698901500225X/hb7345sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S205698901500225X/hb7345Isup2.hkl

Supporting information file. DOI: 10.1107/S205698901500225X/hb7345Isup3.cml

checkCIF report

Comment top

Coumarins and their natural synthetic derivatives are pharmacologically interesting compounds due to their structural diversity and synthetic accessibility (Borges et al., 2005, 2009). Cancer, a diverse group of diseases characterized by uncontrolled growth of abnormal cells, is a major worldwide problem. It is a fatal disease standing next to the cardiovascular disease in terms of morbidity and mortality. Although the cancer research has led to a number of new and effective solutions, the medicines used as treatments have clear limitations and unfortunately cancer is projected as the primary cause of death in the future(Gibbs et al. 2000; Varmus et al. 2006).

The title compound, Fig. 1, consists of a chromene moiety attached to a nitrophenyl ring, a nitro group and a methylamine group. The molecular structure is stabilized by an intra molecular N1—H1A···O5 interaction, which generates an S(6) ring motif. The chromen ring is almost coplanar with the least-square planes of the phenyl ring, making dihedral angle of 87.18 (8)°. The six-membered pyran ring(C7/O1/C8/C10/C11/C12) adopts sofa conformatons, with puckering parameters Q₂ = 0.1787 (17) Å, Q₃ = -0.0688 (18) Å and ϕ₂ = 0.9 (6)°, respectively. The C18 atom deviates from mean plane of the phenyl ring by -0.0260 Å. The title compound exihibits structural similarities with an already reported related structure (Narayanan et al. 2013).

In the crystal, the molecules are linked via intermolecular C9—H9C···O4 hydrogen-bond interaction to generate [010] chains.

Related literature top

For background to the biological activity of chromene derivatives, see: Borges et al. (2005, 2009); Gibbs (2000); Varmus (2006). For a related structure, see: Narayanan et al. (2013).

Experimental top

A solution of 4-methylbenzaldehyde (1.0 mmol), 4-hydroxycoumarin (1.0 mmol), NMSM (1.0 mmol), and piperidine (0.2 equiv) in EtOH (2 ml) was stirred for the three hours. After reaction was complete as indicated by TLC, the product was filtered and washed with EtOH (2 ml) to remove the excess base and other impurities. Finally, the product was recrystallized from EtOH to yield colourless blocks of the title compound.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title molecule, with atom displacement ellipsoids drawn at the 30% probability level. The intramolecular N—H···O hydrogen bond, which generates an S(6) ring motif, is shown as a dashed line.
	Fig. 2. The crystal packing of the title compound, viewed along the b axis, showing C9—H9C···O4 hydrogen bonds producing chains parallel to the 101 planes.

2-Methylamino-3-nitro-4-p-tolylpyrano[3,2-c]chromen-5(4H)-one top

Crystal data top

C₂₀H₁₆N₂O₅	F(000) = 760
M_r = 364.35	D_x = 1.454 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2862 reflections
a = 10.8336 (11) Å	θ = 2.1–30.3°
b = 11.7927 (11) Å	µ = 0.11 mm⁻¹
c = 13.7275 (14) Å	T = 293 K
β = 108.357 (2)°	Block, colourless
V = 1664.5 (3) Å³	0.21 × 0.19 × 0.18 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD diffractometer	4571 independent reflections
Radiation source: fine-focus sealed tube	2862 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
ω and ϕ scans	θ_max = 30.3°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −15→15
T_min = 0.978, T_max = 0.981	k = −15→16
28712 measured reflections	l = −19→19

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.151	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0607P)² + 0.7266P] where P = (F_o² + 2F_c²)/3
4571 reflections	(Δ/σ)_max = 0.001
244 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

C₂₀H₁₆N₂O₅	V = 1664.5 (3) Å³
M_r = 364.35	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.8336 (11) Å	µ = 0.11 mm⁻¹
b = 11.7927 (11) Å	T = 293 K
c = 13.7275 (14) Å	0.21 × 0.19 × 0.18 mm
β = 108.357 (2)°

Data collection top

Bruker SMART APEXII CCD diffractometer	4571 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	2862 reflections with I > 2σ(I)
T_min = 0.978, T_max = 0.981	R_int = 0.039
28712 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.151	H-atom parameters constrained
S = 1.03	Δρ_max = 0.26 e Å⁻³
4571 reflections	Δρ_min = −0.36 e Å⁻³
244 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.39731 (17)	0.29273 (15)	0.11931 (14)	0.0394 (4)
C2	0.3614 (2)	0.18037 (17)	0.11445 (17)	0.0525 (5)
H2	0.2802	0.1594	0.1181	0.063*
C3	0.4481 (2)	0.09986 (18)	0.10411 (18)	0.0569 (6)
H3	0.4256	0.0235	0.1014	0.068*
C4	0.5677 (2)	0.13063 (17)	0.09769 (17)	0.0538 (5)
H4	0.6246	0.0751	0.0895	0.065*
C5	0.60377 (19)	0.24263 (17)	0.10328 (15)	0.0455 (4)
H5	0.6849	0.2629	0.0990	0.055*
C6	0.51827 (16)	0.32599 (14)	0.11533 (13)	0.0358 (4)
C7	0.54773 (16)	0.44453 (14)	0.13040 (13)	0.0342 (4)
C8	0.70721 (17)	0.58447 (15)	0.13873 (13)	0.0375 (4)
C9	0.9063 (2)	0.5072 (2)	0.11560 (18)	0.0560 (5)
H9A	0.9850	0.5386	0.1089	0.084*
H9B	0.8626	0.4640	0.0553	0.084*
H9C	0.9270	0.4587	0.1747	0.084*
C10	0.62572 (17)	0.66705 (14)	0.15559 (13)	0.0365 (4)
C11	0.50320 (16)	0.64000 (14)	0.18012 (13)	0.0359 (4)
H11	0.4340	0.6918	0.1422	0.043*
C12	0.46442 (16)	0.52058 (15)	0.14680 (13)	0.0350 (4)
C13	0.33590 (17)	0.48409 (16)	0.14373 (14)	0.0422 (4)
C14	0.52303 (15)	0.65125 (14)	0.29503 (13)	0.0331 (4)
C15	0.60210 (17)	0.57475 (15)	0.36318 (14)	0.0400 (4)
H15	0.6410	0.5159	0.3384	0.048*
C16	0.62389 (18)	0.58497 (16)	0.46753 (15)	0.0445 (4)
H16	0.6773	0.5328	0.5120	0.053*
C17	0.56764 (17)	0.67147 (16)	0.50698 (14)	0.0414 (4)
C18	0.5931 (2)	0.6825 (2)	0.62041 (16)	0.0597 (6)
H18A	0.6515	0.6236	0.6554	0.090*
H18B	0.5127	0.6760	0.6354	0.090*
H18C	0.6316	0.7552	0.6431	0.090*
C19	0.48681 (18)	0.74572 (16)	0.43833 (15)	0.0449 (4)
H19	0.4466	0.8037	0.4630	0.054*
C20	0.46409 (17)	0.73612 (15)	0.33388 (14)	0.0405 (4)
H20	0.4087	0.7872	0.2894	0.049*
N1	0.82208 (16)	0.59828 (15)	0.12756 (13)	0.0480 (4)
H1	0.8497	0.6666	0.1273	0.058*
N2	0.66129 (17)	0.78014 (13)	0.15862 (12)	0.0455 (4)
O1	0.67089 (11)	0.47326 (10)	0.13148 (10)	0.0405 (3)
O2	0.30759 (12)	0.37082 (11)	0.12920 (11)	0.0469 (3)
O3	0.25155 (13)	0.54490 (13)	0.15308 (14)	0.0624 (4)
O4	0.58643 (16)	0.85218 (12)	0.17480 (12)	0.0591 (4)
O5	0.76697 (15)	0.80934 (12)	0.14575 (12)	0.0598 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0360 (9)	0.0392 (9)	0.0391 (9)	0.0006 (7)	0.0063 (7)	−0.0084 (7)
C2	0.0418 (10)	0.0437 (11)	0.0668 (14)	−0.0075 (8)	0.0098 (9)	−0.0126 (10)
C3	0.0534 (12)	0.0367 (10)	0.0722 (15)	−0.0048 (9)	0.0077 (10)	−0.0144 (10)
C4	0.0517 (12)	0.0410 (11)	0.0642 (13)	0.0066 (9)	0.0117 (10)	−0.0147 (9)
C5	0.0421 (10)	0.0443 (11)	0.0492 (11)	0.0049 (8)	0.0129 (8)	−0.0096 (8)
C6	0.0367 (9)	0.0356 (9)	0.0325 (9)	0.0017 (7)	0.0073 (7)	−0.0051 (7)
C7	0.0324 (8)	0.0367 (9)	0.0324 (8)	0.0011 (7)	0.0089 (7)	−0.0012 (7)
C8	0.0418 (9)	0.0384 (9)	0.0338 (9)	0.0000 (7)	0.0140 (7)	0.0048 (7)
C9	0.0470 (11)	0.0626 (13)	0.0669 (14)	0.0091 (10)	0.0301 (10)	0.0089 (11)
C10	0.0412 (9)	0.0320 (8)	0.0374 (9)	0.0011 (7)	0.0139 (7)	0.0033 (7)
C11	0.0342 (8)	0.0303 (8)	0.0417 (9)	0.0059 (7)	0.0097 (7)	0.0013 (7)
C12	0.0332 (8)	0.0357 (9)	0.0342 (9)	0.0034 (7)	0.0079 (7)	−0.0016 (7)
C13	0.0346 (9)	0.0415 (10)	0.0470 (10)	0.0018 (7)	0.0081 (8)	−0.0061 (8)
C14	0.0298 (8)	0.0308 (8)	0.0402 (9)	−0.0002 (6)	0.0131 (7)	−0.0001 (7)
C15	0.0393 (9)	0.0360 (9)	0.0457 (10)	0.0082 (7)	0.0149 (8)	−0.0012 (7)
C16	0.0436 (10)	0.0439 (10)	0.0438 (10)	0.0067 (8)	0.0107 (8)	0.0084 (8)
C17	0.0385 (9)	0.0442 (10)	0.0441 (10)	−0.0077 (8)	0.0165 (8)	−0.0041 (8)
C18	0.0679 (14)	0.0687 (15)	0.0450 (12)	−0.0062 (11)	0.0212 (10)	−0.0041 (10)
C19	0.0460 (10)	0.0415 (10)	0.0517 (11)	0.0046 (8)	0.0220 (9)	−0.0075 (8)
C20	0.0385 (9)	0.0366 (9)	0.0466 (10)	0.0071 (7)	0.0138 (8)	−0.0001 (8)
N1	0.0472 (9)	0.0462 (9)	0.0595 (10)	−0.0008 (7)	0.0295 (8)	0.0051 (8)
N2	0.0586 (10)	0.0366 (8)	0.0424 (9)	−0.0015 (7)	0.0176 (8)	0.0045 (7)
O1	0.0364 (6)	0.0360 (7)	0.0525 (8)	0.0021 (5)	0.0189 (6)	−0.0005 (6)
O2	0.0344 (6)	0.0419 (7)	0.0626 (9)	−0.0018 (5)	0.0129 (6)	−0.0120 (6)
O3	0.0376 (7)	0.0541 (9)	0.0952 (12)	0.0077 (6)	0.0204 (8)	−0.0142 (8)
O4	0.0780 (10)	0.0349 (7)	0.0708 (10)	0.0064 (7)	0.0328 (8)	0.0035 (7)
O5	0.0682 (10)	0.0461 (8)	0.0738 (11)	−0.0111 (7)	0.0348 (8)	0.0063 (7)

Geometric parameters (Å, º) top

C1—O2	1.376 (2)	C11—C12	1.499 (2)
C1—C2	1.377 (3)	C11—C14	1.529 (2)
C1—C6	1.385 (2)	C11—H11	0.9800
C2—C3	1.374 (3)	C12—C13	1.445 (2)
C2—H2	0.9300	C13—O3	1.200 (2)
C3—C4	1.374 (3)	C13—O2	1.371 (2)
C3—H3	0.9300	C14—C20	1.381 (2)
C4—C5	1.373 (3)	C14—C15	1.385 (2)
C4—H4	0.9300	C15—C16	1.382 (3)
C5—C6	1.396 (2)	C15—H15	0.9300
C5—H5	0.9300	C16—C17	1.383 (3)
C6—C7	1.434 (2)	C16—H16	0.9300
C7—C12	1.341 (2)	C17—C19	1.379 (3)
C7—O1	1.372 (2)	C17—C18	1.499 (3)
C8—N1	1.311 (2)	C18—H18A	0.9600
C8—O1	1.364 (2)	C18—H18B	0.9600
C8—C10	1.382 (2)	C18—H18C	0.9600
C9—N1	1.452 (3)	C19—C20	1.381 (3)
C9—H9A	0.9600	C19—H19	0.9300
C9—H9B	0.9600	C20—H20	0.9300
C9—H9C	0.9600	N1—H1	0.8600
C10—N2	1.385 (2)	N2—O4	1.242 (2)
C10—C11	1.503 (2)	N2—O5	1.260 (2)

O2—C1—C2	116.81 (17)	C7—C12—C13	119.29 (16)
O2—C1—C6	121.38 (16)	C7—C12—C11	122.74 (15)
C2—C1—C6	121.81 (17)	C13—C12—C11	117.61 (15)
C3—C2—C1	118.54 (19)	O3—C13—O2	117.06 (17)
C3—C2—H2	120.7	O3—C13—C12	125.32 (18)
C1—C2—H2	120.7	O2—C13—C12	117.62 (15)
C2—C3—C4	120.87 (19)	C20—C14—C15	118.29 (16)
C2—C3—H3	119.6	C20—C14—C11	121.95 (15)
C4—C3—H3	119.6	C15—C14—C11	119.76 (15)
C5—C4—C3	120.53 (19)	C16—C15—C14	120.72 (16)
C5—C4—H4	119.7	C16—C15—H15	119.6
C3—C4—H4	119.7	C14—C15—H15	119.6
C4—C5—C6	119.76 (19)	C15—C16—C17	121.18 (17)
C4—C5—H5	120.1	C15—C16—H16	119.4
C6—C5—H5	120.1	C17—C16—H16	119.4
C1—C6—C5	118.46 (17)	C19—C17—C16	117.64 (17)
C1—C6—C7	116.14 (15)	C19—C17—C18	121.61 (18)
C5—C6—C7	125.29 (17)	C16—C17—C18	120.75 (19)
C12—C7—O1	122.46 (16)	C17—C18—H18A	109.5
C12—C7—C6	123.04 (16)	C17—C18—H18B	109.5
O1—C7—C6	114.43 (14)	H18A—C18—H18B	109.5
N1—C8—O1	111.93 (16)	C17—C18—H18C	109.5
N1—C8—C10	127.74 (17)	H18A—C18—H18C	109.5
O1—C8—C10	120.33 (15)	H18B—C18—H18C	109.5
N1—C9—H9A	109.5	C17—C19—C20	121.64 (17)
N1—C9—H9B	109.5	C17—C19—H19	119.2
H9A—C9—H9B	109.5	C20—C19—H19	119.2
N1—C9—H9C	109.5	C19—C20—C14	120.49 (17)
H9A—C9—H9C	109.5	C19—C20—H20	119.8
H9B—C9—H9C	109.5	C14—C20—H20	119.8
C8—C10—N2	119.80 (16)	C8—N1—C9	125.09 (17)
C8—C10—C11	122.95 (15)	C8—N1—H1	117.5
N2—C10—C11	117.04 (15)	C9—N1—H1	117.5
C12—C11—C10	108.26 (14)	O4—N2—O5	120.76 (16)
C12—C11—C14	109.33 (14)	O4—N2—C10	118.21 (16)
C10—C11—C14	111.45 (14)	O5—N2—C10	121.03 (16)
C12—C11—H11	109.3	C8—O1—C7	119.69 (13)
C10—C11—H11	109.3	C13—O2—C1	122.25 (14)
C14—C11—H11	109.3

O2—C1—C2—C3	179.72 (18)	C11—C12—C13—O3	9.9 (3)
C6—C1—C2—C3	−0.8 (3)	C7—C12—C13—O2	3.3 (3)
C1—C2—C3—C4	−0.6 (3)	C11—C12—C13—O2	−169.93 (15)
C2—C3—C4—C5	1.1 (3)	C12—C11—C14—C20	−129.00 (17)
C3—C4—C5—C6	−0.2 (3)	C10—C11—C14—C20	111.35 (18)
O2—C1—C6—C5	−178.80 (16)	C12—C11—C14—C15	51.0 (2)
C2—C1—C6—C5	1.7 (3)	C10—C11—C14—C15	−68.7 (2)
O2—C1—C6—C7	4.9 (2)	C20—C14—C15—C16	−1.6 (3)
C2—C1—C6—C7	−174.59 (18)	C11—C14—C15—C16	178.42 (16)
C4—C5—C6—C1	−1.2 (3)	C14—C15—C16—C17	0.0 (3)
C4—C5—C6—C7	174.73 (18)	C15—C16—C17—C19	1.4 (3)
C1—C6—C7—C12	−0.5 (3)	C15—C16—C17—C18	−179.30 (18)
C5—C6—C7—C12	−176.51 (18)	C16—C17—C19—C20	−1.2 (3)
C1—C6—C7—O1	176.64 (15)	C18—C17—C19—C20	179.47 (18)
C5—C6—C7—O1	0.6 (3)	C17—C19—C20—C14	−0.4 (3)
N1—C8—C10—N2	2.4 (3)	C15—C14—C20—C19	1.8 (3)
O1—C8—C10—N2	−177.36 (15)	C11—C14—C20—C19	−178.26 (16)
N1—C8—C10—C11	−172.24 (17)	O1—C8—N1—C9	−3.8 (3)
O1—C8—C10—C11	8.0 (3)	C10—C8—N1—C9	176.42 (19)
C8—C10—C11—C12	−19.5 (2)	C8—C10—N2—O4	−179.39 (17)
N2—C10—C11—C12	165.70 (15)	C11—C10—N2—O4	−4.5 (2)
C8—C10—C11—C14	100.73 (19)	C8—C10—N2—O5	0.3 (3)
N2—C10—C11—C14	−74.03 (19)	C11—C10—N2—O5	175.25 (16)
O1—C7—C12—C13	179.56 (15)	N1—C8—O1—C7	−173.09 (15)
C6—C7—C12—C13	−3.6 (3)	C10—C8—O1—C7	6.7 (2)
O1—C7—C12—C11	−7.6 (3)	C12—C7—O1—C8	−7.0 (2)
C6—C7—C12—C11	169.29 (16)	C6—C7—O1—C8	175.86 (15)
C10—C11—C12—C7	19.3 (2)	O3—C13—O2—C1	−178.85 (17)
C14—C11—C12—C7	−102.29 (19)	C12—C13—O2—C1	1.0 (3)
C10—C11—C12—C13	−167.72 (15)	C2—C1—O2—C13	174.23 (17)
C14—C11—C12—C13	70.70 (19)	C6—C1—O2—C13	−5.2 (3)
C7—C12—C13—O3	−176.84 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O5	0.86	1.96	2.590 (2)	129
C9—H9C···O4ⁱ	0.96	2.46	3.389 (3)	163

Symmetry code: (i) −x+3/2, y−1/2, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O5	0.86	1.96	2.590 (2)	129
C9—H9C···O4ⁱ	0.96	2.46	3.389 (3)	163

Symmetry code: (i) −x+3/2, y−1/2, −z+1/2.

Acknowledgements

The authors thank Dr Babu Varghese, SAIF, IIT, Chennai, India, for the data collection.

References

Borges, F., Roleira, F., Milhazes, N., Santana, L. & Uriarte, E. (2005). Curr. Med. Chem. 12, 887–916. Web of Science CrossRef PubMed CAS Google Scholar
Borges, F., Roleira, F., Milhazes, N., Uriarte, E. & Santana, L. (2009). Front. Med. Chem. 4, 23–85. Google Scholar
Bruker (2008). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Gibbs, J. B. (2000). Science, 287, 1969–1973. Web of Science CrossRef PubMed CAS Google Scholar
Narayanan, P., Kamalraja, J., Perumal, P. T. & Sethusankar, K. (2013). Acta Cryst. E69, o931–o932. CSD CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Varmus, H. (2006). Science, 312, 1162–1165. Web of Science CrossRef PubMed CAS Google Scholar

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Volume 71| Part 3| March 2015| Pages o158-o159

doi:10.1107/S205698901500225X

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structure of 2-methyl­amino-3-nitro-4-p-tolyl­pyrano[3,2-c]chromen-5(4H)-one

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of 2-methylamino-3-nitro-4-p-tolylpyrano[3,2-c]chromen-5(4H)-one